Create a recurring listing option within my theme

I currently use Vantage theme from Wordpress and am frustrated at the lack of a way to allow my customers to renew their listing. Your job will be to add a method that will allow people to renew their listing when it expires, tied in with Pay Pal. It will need to have the ability to email a customer when their listing is close to expiring at 30 days, 15 days, 5 days and the day of expiration. Currently, if a listing expires, it is deleted from the database. I want the post to simple be reset to pending so it doesn't disappear from the back end, and does not show on the front end. I also need something that will allow the user to see click-thrus of their listing to their website This will have to be done within a child theme Vantage is a funky theme to work with, so know what you are talking about when bidding.